DE1620483A1 - Verfahren zu der Herstellung eines alpha-Nitro-omega-lactams - Google Patents
Verfahren zu der Herstellung eines alpha-Nitro-omega-lactamsInfo
- Publication number
- DE1620483A1 DE1620483A1 DE19661620483 DE1620483A DE1620483A1 DE 1620483 A1 DE1620483 A1 DE 1620483A1 DE 19661620483 DE19661620483 DE 19661620483 DE 1620483 A DE1620483 A DE 1620483A DE 1620483 A1 DE1620483 A1 DE 1620483A1
- Authority
- DE
- Germany
- Prior art keywords
- solvent
- nitro
- sulfur trioxide
- reaction
- hydrolysis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 3
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 18
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims description 13
- 230000007062 hydrolysis Effects 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- -1 sulfuric acid ester Chemical class 0.000 claims description 7
- 238000006396 nitration reaction Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 5
- 230000000802 nitrating effect Effects 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical class C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6501881A NL6501881A (enrdf_load_stackoverflow) | 1965-02-16 | 1965-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1620483A1 true DE1620483A1 (de) | 1970-04-09 |
Family
ID=19792373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661620483 Pending DE1620483A1 (de) | 1965-02-16 | 1966-02-16 | Verfahren zu der Herstellung eines alpha-Nitro-omega-lactams |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3448103A (enrdf_load_stackoverflow) |
| AT (1) | AT261569B (enrdf_load_stackoverflow) |
| BE (1) | BE676511A (enrdf_load_stackoverflow) |
| CH (1) | CH473810A (enrdf_load_stackoverflow) |
| DE (1) | DE1620483A1 (enrdf_load_stackoverflow) |
| ES (1) | ES323101A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1126853A (enrdf_load_stackoverflow) |
| NL (2) | NL6501881A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987034A (en) * | 1974-03-11 | 1976-10-19 | Idaho Research Foundation, Inc. | Process for the preparation of tetrazocine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3096326A (en) * | 1963-07-02 | Preparation of a-nixro e-caprolactam |
-
0
- NL NL129861D patent/NL129861C/xx active
-
1965
- 1965-02-16 NL NL6501881A patent/NL6501881A/xx unknown
-
1966
- 1966-02-14 GB GB6433/66A patent/GB1126853A/en not_active Expired
- 1966-02-15 AT AT137566A patent/AT261569B/de active
- 1966-02-15 BE BE676511D patent/BE676511A/xx unknown
- 1966-02-15 ES ES0323101A patent/ES323101A1/es not_active Expired
- 1966-02-16 CH CH222466A patent/CH473810A/de not_active IP Right Cessation
- 1966-02-16 US US527837A patent/US3448103A/en not_active Expired - Lifetime
- 1966-02-16 DE DE19661620483 patent/DE1620483A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES323101A1 (es) | 1966-12-01 |
| CH473810A (de) | 1969-06-15 |
| GB1126853A (en) | 1968-09-11 |
| AT261569B (de) | 1968-05-10 |
| US3448103A (en) | 1969-06-03 |
| BE676511A (enrdf_load_stackoverflow) | 1966-08-16 |
| NL129861C (enrdf_load_stackoverflow) | |
| NL6501881A (enrdf_load_stackoverflow) | 1966-08-17 |
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